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Volume 21, Issue 5-6, Pages 293-303

On the prenylation of some indolic and imidazolic bases by oxirane auxiliaries under thermal and microwave conditions

Christopher K. Jankowski,1 Etienne Dako,1 Antoun Bou Laouz,1 Marcel Delaforge,2 Jocelyn R. J. Paré,3 and Jacqueline M. R. Belanger3

1Département de chimie et biochimie, Université de Moncton, Moncton, NB E1A 3E9, Canada
2CEA Saclay, iBiTec-S, URA2096, Gif sur Yvette, F-91191, France
3Environment Canada, Green Technologies Division, 335 River Road, Ottawa, ON K1A 0H3, Canada

Copyright © 2007 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


The analogue of isoprene, 2-methyl-2-vinyloxirane, a versatile isoprene auxiliary, was reacted with some indolic and imidazolic bases, to add one or more isoprene unit(s), to these compounds. This prenylation was realised by using thermal and microwave assisted pathways, via the nucleophilic opening of the epoxide ring. The biological importance of the prenylated derivatives resides in their potential application as drugs. The aminoacids and small protein biomarkers are obtained from simple epoxide opening reactions. All new compounds were characterised by high resolution NMR, mass spectroscopy, GC-MS and LC-MS as well.